| 100% | ASBRAVEASYOU | 12 | 29-Across novel that won the Kirkus Prize in 2016 and the NAACP Image Award for Outstanding Literary Work for Youth/Teen in 2017 (4 wds.) |
| 45% | BLONDEFAITH | 11 | 2007 novel featuring 17-Across for which 29-Across won the NAACP Image Award for Outstanding Literary Work, Fiction (2 wds.) |
| 39% | ASBRAVEASYOU | 12 | 2016 novel by 30-Across that won the Kirkus Prize: 4 wds. |
| 35% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 34% | KNOWNOBETTER | 12 | Major Lazer song featuring Travis Scott, Camila Cabello, and Quavo that won the 2017 Teen Choice Award for Choice Electronic/Dance Song (3 wds.) |
| 33% | BEFORETHEFALL | 13 | Noah Hawley novel that won the 2017 Edgar Award for Best Novel (3 wds.) |
| 33% | THEROUNDHOUSE | 13 | Louise Erdrich novel that won the National Book Award for Fiction in 2012 (3 wds.) |
| 33% | LORDOFMISRULE | 13 | Jaimy Gordon novel that won the National Book Award for Fiction in 2010 (3 wds.) |
| 33% | SAMUELLJACKSON | 14 | Actor who has earned four NAACP Image Awards, for his work in 19-Across, 46-Across, "Mother and Child," and "Django Unchained" (3 wds.) |
| 33% | LITTLEBIGTOWN | 13 | 15-Across and 54-Across band that won the 2017 Country Music Association Award for Vocal Group of the Year (3 wds.) |
| 32% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 32% | ANNPATCHETT | 11 | 15-Across and 43-Across writer who won the Orange Prize for Fiction and the PEN/Faulkner Award for Fiction for "Bel Canto" (2 wds.) |
| 32% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 32% | DAVIDOYELOWO | 12 | 19-Across and 33-Across actor who won a 2015 NAACP Image Award for his portrayal of Martin Luther King Jr. in "Selma" (2 wds.) |
| 31% | ANNAQUINDLEN | 12 | "One True Thing," 14-Across, and 26-Across/29-Across novelist who won the Pulitzer Prize for Commentary in 1992 (2 wds.) |
| 31% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 31% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 31% | GABRIELLEZEVIN | 14 | 16-Across and 28-Across writer whose novel "Tomorrow, and Tomorrow, and Tomorrow" won the Goodreads Choice Award Winner for Best Fiction in 2022 (2 wds.) |
| 31% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 31% | STUDIOCITY | 10 | Series about a fictional soap opera that won the Daytime Emmy Award for Outstanding Limited Drama Series in 2021 (2 wds.) |
| 31% | DONTLETMEDOWN | 13 | The Chainsmokers song that won the 2017 Grammy Award for Best Dance Recording (4 wds.) |
| 30% | THESEAAROUNDUS | 14 | 44-Across book about the science and history of the ocean that won the 1952 National Book Award for Nonfiction (4 wds.) |
| 30% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 30% | GAMEOFTHRONES | 13 | HBO fantasy show that won Primetime Emmys for Outstanding Drama Series in 2015, 2016, 2018, and 2019 (3 wds.) |
| 30% | RULEOFWOLVES | 12 | Novel by 40-Across that won the 2021 Goodreads Choice Award for Young Adult Fantasy (3 wds.) |
| 30% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 30% | ELISABETHMOSS | 13 | "The Handmaid's Tale" star who won the 2017 Emmy Award for Outstanding Lead Actress in a Drama Series (2 wds.) |
| 30% | BROWN | 5 | "Murphy ___," TV sitcom that won the Emmy Award for Outstanding Comedy Series in 1990 and 1992 |
| 30% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 30% | LEIGHBARDUGO | 12 | 18-Across and 29-Across writer whose novel "Ninth House" won the 2019 Goodreads Choice Award for Best Fantasy (2 wds.) |